Antiseptic anaesthetic salts



Patented Apr. 9, 1929.

PATENT OFFICE.

BLUFF,

ILLINOIS, A CORPORATION OF ILLINOIS.

ANTISEPTIC .ANESTHE'I'IC SALTS.

No Drawing. Application filed July 25,

As is well known, many substances possess pronounced local anaestheticproperties, but

very few of themsare capable of exerting effective antiseptic action.Such antiseptic action is particularly desirable, due to the fact thatlocal anaesthetics are frequently employed for topical application toareas which are abraded or otherwise injured so that infection is likelyto result if an efiicient antiseptic is not available. The uses ofmixtures of many local anaesthetics and antiseptics is oftenundesirable, because of incompatibilities between the two types ofcompounds, and because of the inconvenience of application of severalmedicaments in succession.

In the preparation of compounds possessing both antiseptic andanaesthetic power, difiiculties ordinarily arise, due to the fact thatchemical combination between the components will not take place. Forexample, ananaesthetic such as salicyl alcohol cannot be made to combinewith an antiseptic like phenol; andeven when chemical combinations ofthe desired nature are accomplished, the resulting products havefrequently lost one or both of the requisite therapeutic properties.

We have found that it is possible to make salts by combiningn-butyl-p-aminobenzoate with halogenated aromatic sulfonic acidscontaining a phenolic hydroxyl group; the resultant products areeffective as local anaesthetics for topical application, and exertpronounced antiseptic action aswell. The desired reaction may be broughtabout by dissolving the anaesthetic and the antiseptic I separately insuitable solvents, mixing the solutions to produce the reaction, andfiltering off the compound which separates from solution as a result ofthe reaction. Various solvents may'be employed, and we do not limitourselves to the particular method out lined here. The compounds s0produced are represented by the formula mmoooOrrmno-n 1927. Serial No.208,408.

Example I Para amino n buty Z benzoate salt of2,6-di-z'0d0piwn0Z-4-suZf0ni0 acid.

formed. The crystals are filtered and washed with Water. Afterrecrystallization from dilute alcohol, this product melts, withdecomposition, at 200 C. ,It is only slightly soluble in water, has alight yellowish-gray color, and exerts strong anaesthetic and antisepticaction.

Example I I Para-amino n butyl benzoaz e salt 0 fQfidibromophen0Z-4-sulf0ni0 acid.

Br I

'The reaction may be carried out as described in Example I, 25 grams ofthe sulfate of para-amino-n-butyl-benzoate in 200 cc. hot water, and 37grams of the potassium salt of 2,6-dibromophenoll-sulfonic acid in 300cc. hot water being employed. Crystallization takes place quickly,particularly when inoculated. The solid is filtered and washed withwater or with small amounts of alcohol and ether. The product is a whitesolid, melting at 216218 0., sparingly soluble in water, and having astrong anaesthetic and antiseptic action.

Emample III. Pam-amino-n-butyl benzoate salt of 7-z'00l0-8-Md'romy-guinoline-5-sulfom'c acid.

(N) mmoooO-Nm.

7 grams of the sulfonic acid is dissolved in hot ammonium hydroxidesolution and added to a hot aqueous solution of 5 grams of the sulfateof para-amino-n-butyl benzoate, the latter containing a little excesssulfuric acid. An oil separates, and on cooling solidifies to a mass oforange crystals. Upon recrystallization from 50% alcohol, the product isobtained as orange crystals which melt at 235240 C. The product issparingly soluble in water, and is a powerful anaesthetic with strongantiseptic genated aromatic sulfonic acid containing a phenolic hydroxylgroup. 7

2. As anew article of manufacture, an

' anaesthetic-antiseptic compound of n-butyl-pamino benzoate and ahalogenated phenol sulfonic acid. 1

3. As a new article of manufacture, an

anaesthetic-antiseptic compound of n-butyl-pamino benzoate and aniodinated phenol sulfonic acid.

4. As a new article of manufacture, an anaesthetic-antiseptic compoundof n-butyl-palniino benzoate and a di-iodophenol sulfonic ac1 5. As anew anaesthetic-antiseptic compound, the salt of n-butyl-p-aminobenzoate and 2,6-di-iodophenol-4-sulfonic acid, and

having the structure (n) mmoocO-rrmnoQsom which is a white solid,melting at 200 C.

with decomposition, almost insoluble in 1 water, but soluble in certainvegetable oils, as well as in other organic solvents.

July 20,1927.

ERNEST H. VOLVVILER. DONALEE L. TABERN.

